Coronaridine

CAS# 467-77-6

Coronaridine

2D Structure

Catalog No. BCN3762----Order now to get a substantial discount!

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Quality Control of Coronaridine

3D structure

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Coronaridine

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Chemical Properties of Coronaridine

Cas No. 467-77-6 SDF Download SDF
PubChem ID 6426909 Appearance Powder
Formula C21H26N2O2 M.Wt 338.4
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms (-)-Coronaridine
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name methyl (1S,15R,17S,18S)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene-1-carboxylate
SMILES CCC1CC2CC3(C1N(C2)CCC4=C3NC5=CC=CC=C45)C(=O)OC
Standard InChIKey NVVDQMVGALBDGE-PZXGUROGSA-N
Standard InChI InChI=1S/C21H26N2O2/c1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18/h4-7,13-14,19,22H,3,8-12H2,1-2H3/t13-,14+,19+,21-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Coronaridine

The herbs of Ervatamia divaricata

Biological Activity of Coronaridine

Description1. Coronaridine is an antitumor agent. 2. Coronaridine congeners inhibit hα3β4 AChRs by blocking the ion channel's lumen and probably by additional negative allosteric mechanisms by interacting with a series of non-luminal sites.
TargetsAChR

Coronaridine Dilution Calculator

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Coronaridine Molarity Calculator

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Preparing Stock Solutions of Coronaridine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.9551 mL 14.7754 mL 29.5508 mL 59.1017 mL 73.8771 mL
5 mM 0.591 mL 2.9551 mL 5.9102 mL 11.8203 mL 14.7754 mL
10 mM 0.2955 mL 1.4775 mL 2.9551 mL 5.9102 mL 7.3877 mL
50 mM 0.0591 mL 0.2955 mL 0.591 mL 1.182 mL 1.4775 mL
100 mM 0.0296 mL 0.1478 mL 0.2955 mL 0.591 mL 0.7388 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Coronaridine

Coronaridine congeners inhibit human alpha3beta4 nicotinic acetylcholine receptors by interacting with luminal and non-luminal sites.[Pubmed:26022277]

Int J Biochem Cell Biol. 2015 Aug;65:81-90.

To characterize the interaction of Coronaridine congeners with human (h) alpha3beta4 nicotinic acetylcholine receptors (AChRs), structural and functional approaches were used. The Ca(2+) influx results established that Coronaridine congeners noncompetitively inhibit halpha3beta4 AChRs with the following potency (IC50's in muM) sequence: (-)-ibogamine (0.62+/-0.23) approximately (+)-catharanthine (0.68+/-0.10)>(-)-ibogaine (0.95+/-0.10)>(+/-)-18-methoxyCoronaridine [(+/-)-18-MC] (1.47+/-0.21)>(-)-voacangine (2.28+/-0.33)>(+/-)-18-methylaminoCoronaridine (2.62+/-0.57 muM) approximately (+/-)-18-hydroxyCoronaridine (2.81+/-0.54)>(-)-noribogaine (6.82+/-0.78). A good linear correlation (r(2)=0.771) between the calculated IC50 values and their polar surface area was found, suggesting that this is an important structural feature for its activity. The radioligand competition results indicate that (+/-)-18-MC and (-)-ibogaine partially inhibit [(3)H]imipramine binding by an allosteric mechanism. Molecular docking, molecular dynamics, and in silico mutation results suggest that protonated (-)-18-MC binds to luminal [i.e., beta4-Phe255 (phenylalanine/valine ring; position 13'), and alpha3-Leu250 and beta4-Leu251 (leucine ring; position 9')], non-luminal, and intersubunit sites. The pharmacophore model suggests that nitrogens from the ibogamine core as well as methylamino, hydroxyl, and methoxyl moieties at position 18 form hydrogen bonds. Collectively our data indicate that Coronaridine congeners inhibit halpha3beta4 AChRs by blocking the ion channel's lumen and probably by additional negative allosteric mechanisms by interacting with a series of non-luminal sites.

Cytotoxicity and genotoxicity of coronaridine from Tabernaemontana catharinensis A.DC in a human laryngeal epithelial carcinoma cell line (Hep-2).[Pubmed:23569415]

Genet Mol Biol. 2013 Mar;36(1):105-10.

Cancer has become a major public health problem worldwide and the number of deaths due to this disease is increasing almost exponentially. In the constant search for new treatments, natural products of plant origin have provided a variety of new compounds to be explored as antitumor agents. Tabernaemontana catharinensis is a medicinal plant that produces alkaloids with expressive antitumor activity, such as heyneanine, Coronaridine and voacangine. The aim of present study was firstly to screen the cytotoxic activity of the indole alkaloids heyneanine, Coronaridine and voacangine against HeLa (human cervix tumor), 3T3 (normal mouse embryo fibroblasts), Hep-2 (human laryngeal epithelial carcinoma) and B-16 (murine skin) cell lines by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide); and secondly to analyze the apoptotic activity, cell membrane damage and genotoxicity of the compound that showed the best cytotoxic activity against the tumor cell lines tested. Coronaridine was the one that exhibited greater cytotoxic activity in the laryngeal carcinoma cell line Hep-2 (IC50 = 54.47 mug/mL) than the other alkaloids tested (voacangine IC50 = 159.33 g/mL, and heyneanine IC50 = 689.45 mug/mL). Coronaridine induced apoptosis in cell lines 3T3 and Hep-2, even at high concentrations. The evaluation of genotoxicity by comet assay showed further that Coronaridine caused minimal DNA damage in the Hep-2 tumor cell line, and the LDH test showed that it did not affect the plasma membrane. These results suggest that further investigation of Coronaridine as an antitumor agent has merit.

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